Quinoline → 4-bromo-5-methoxy-1H-indole

HRID 1791804ノート

反応式

HRID 1791804 の反応式
[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5](C(O)=O)[NH:6]2.N1C2C(=CC=CC=2)C=CC=1>[Cr]([O-])([O-])=O.[Cu+2]>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

参加物

4

反応物 2

HCID 7047QuinolineHCID 133565154-Bromo-5-methoxy-1H-indole-2-carboxylic acid

生成物 1

HCID 220305584-bromo-5-methoxy-1H-indole収率 67%

試薬・触媒・溶媒 1

HCID 178505374HCID 178505374、化合物触媒

反応条件

温度
245 °C

実験手順

4-Bromo-5-methoxyindole-2-carboxylic acid (1.25 g, 4.19 mmol), quinoline (15 ml) and copper chromite (313 mg) were mixed together. Nitrogen was gently bubbled through the mixture for 5 minutes, then the mixture heated quickly to 245° C. under an atmosphere of nitrogen. After 90 minutes the mixture was cooled to ambient temperature diluted with ethyl acetate (100 ml) and washed with 2M aqueous hydrochloric acid (60 ml). The ethyl acetate layer was filtered, the filtrate dried (MgSO4) and the solvent evaporated. The residue was purified by silica column chromatography eluting with dichloromethane/hexane (1/1) to give 4-bromo-5-methoxyindole (635 mg, 60%).

後処理

  1. customNitrogen was gently bubbled through the mixture for 5 minutes
  2. temperatureAfter 90 minutes the mixture was cooled to ambient temperature
  3. additiondiluted with ethyl acetate (100 ml)
  4. washwashed with 2M aqueous hydrochloric acid (60 ml)
  5. filtrationThe ethyl acetate layer was filtered
  6. dry with materialthe filtrate dried (MgSO4)
  7. customthe solvent evaporated
  8. customThe residue was purified by silica column chromatography
  9. washeluting with dichloromethane/hexane (1/1)

出典と根拠

ORDレコード
ord-d6f2ecd05d344eecbf92022007dacf5d
出典データセット
uspto-grants-2006_07
特許番号
US07074800B1

反応ノート

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